Chestertown, MD Homes for Sale with Hardwood Floors

Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stone’s throw from historic Chestertown, the property combines seclusion with

Julie Santoboni Taylor Properties

Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

William Norris Select Land & Homes, LLC

A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm

Jonathan Taylor Hyatt & Company Real Estate, LLC

HIGHFIELD, has been home to the renown architectural historian MichaelBourne and his family for almost forty-years. Mr. Bourne who authored theimportant Historic Houses of Kent County and guided the restorations of over400 historic structures in the mid-Atlantic, together with his wife, Ann,created a home that reflects their deep appreciation for the refined beauty ofhistoric

Nancy McGuire Maryland Heritage Properties

Stately presence on historic Queen Street! More info & professional photos coming soon!A grand curved staircase acsends all the way to the third floor with large light filled landings. Spread out in generously sized rooms throughout this home. A truly versatile layout! Access the 8'x31' screened in side-porch from the Living room, Dining Room, and large Kitchen! A first floor laundry closet and

Beth Ostrander Doug Ashley Realtors, LLC

Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

Matthew Altizer ANR Realty, LLC

Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom, 2 bath home offers the perfect blend of comfort and modern living and is ideal for quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find yourself within easy reach of local amenities, including parks and trails, the Chester

Jeannette Westcott Keller Williams Realty Centre

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and

Liddy Campbell TTR Sotheby's International Realty

Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

Debbie Meikle Doug Ashley Realtors, LLC

Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside

Doug Ashley Doug Ashley Realtors, LLC

Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

Jeff Guthrie Cross Street Realtors LLC

Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

Jeff Guthrie Cross Street Realtors LLC

Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

Jo Ann Edwards The Hogans Agency

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman-style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately150 feet of shoreline and a sandy beach, this property is a true waterfront gem.**Key Features:**- **Spacious Great

Ashton Kelley Gunther-McClary Real Estate

Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect for a weekend retreat, investment property, or full-time

Sarah King Cross Street Realtors LLC